From Jakarta to Bali to Manila
September 2nd–8th, 2026 · Indonesia + Philippines
Three stops, three very different rooms, and one question that kept getting bigger: if AI is changing this fast, are our organizations, and the humans inside them, actually ready to change with it?
Across Jakarta, Bali, and Manila, People Matters brought Jason into different rooms and formats, from workshops and roundtables to keynotes and conversations that continued long after the sessions ended.
These are the ideas Jason brought home.
Jakarta
The missing layer isn’t another tool. It’s context.
Jakarta started with organisational intelligence, and a problem that sounded familiar almost immediately.
Organizations are sitting on enormous amounts of context: documents, rules, roles, procedures, governance, past decisions, and the tribal knowledge that explains how work actually gets done. They know it's there. What they don't necessarily know is how to turn all of that into something AI can understand and use.
Before the room could get to how to build that context layer, there was an earlier question to answer: why does context matter in the first place?
“AI without context is nothing. It's just a tool.”
Start with the inventory.
What does your organization already know about how work gets done? Where does that knowledge live? Who carries it? What gets written down, and what only exists because somebody has been there for twelve years?
The first step toward organizational intelligence isn’t another implementation. It’s understanding the context you already have.
Bali
Sometimes you have to slow down before you can see what needs to change.
Bali was different.
Jakarta had been action-oriented. Bali was intentionally slower, a leadership retreat built around community, collaboration, reflection, and being together.
Jason walked into Bali nervous. As an introvert, several days inside a deeply connected leadership retreat wasn't exactly his natural habitat. He left with relationships that felt completely different from the ones you build by moving from meeting to meeting.
That became part of the lesson. Transformation asks people to question familiar ways of working, challenge assumptions, and imagine something different. The environment around that work matters. Bali created the time and space for people to learn together, laugh together, disagree, reflect, and build the kind of trust that makes those harder conversations possible.
“We got to learn from each other, grow with each other, laugh with each other, cry with each other.”
2030 problems.
2010 org charts.
1990s processes.
When Jason challenged the room to think about whether organizations built on legacy structures are still fit for what comes next, that framing hit home.
The uncomfortable part wasn't convincing people that work needs to change. They already knew.
The harder question was whether they were actually willing to rebuild it.
AI is an accelerant. It isn’t the answer by itself.
Forget how you do it today.
In The Intelligence Dividend, Jason and Vikrant Khanna pushed the room into beginner’s mindset.
Break the process apart. Ask why it exists. Ask who it is actually for. Then ask what you could do with AI versus what you should do with AI.
That’s where another obstacle became impossible to ignore:
inertia.
Apparently, some processes get funnier when you actually look at them.
Approvals came up. Finance came up. Workflows everyone had inherited came up.
Then people started asking a wonderfully dangerous question:
Why do we do this?
Jason said inertia wasn’t just named and challenged in the room. Eventually, people started laughing at it. Once they actually examined some of the processes they’d accepted as normal, the absurdity became obvious.
The conversations didn’t stop when the sessions did.
Some of what Jason remembers most clearly from Bali didn’t happen on a stage at all.
It was being together. Eating together. Doing the activities together. Laughing together. Having enough time in the same place for a room full of people to stop feeling like a room full of strangers.
What stayed with Jason was something much simpler than a framework: humans being with humans creates value, love, and a kind of connection that is difficult to reproduce through a screen.
People Matters created a WhatsApp group so everyone could stay connected. While telling us about it during this interview, Jason stopped and decided to go say hello to everyone.
Manila
400 people. One variable that mattered most.
Manila brought the ideas from the week into a much bigger room.
Jason’s message was You Are the Variable, and the realization he saw spreading through the audience was simple: organizations have been counting on the tool to do too much of the changing for them.
The technology isn’t the variable.
We are.
“A fool with a tool is still a fool.”
After the keynote, people stopped Jason in the hallway to tell him the message had changed how they were thinking. Several asked whether he could bring it back to their own teams.
Start from scratch.
The hardest part of Making AI Work at Work wasn’t choosing what to automate.
It was getting people to temporarily forget the systems, processes, and assumptions they already had.
Beginner’s mindset sounds easy until someone asks you to imagine the work without everything you’ve inherited.
This is not a systems implementation.
It’s an opportunity to start from scratch.
Humans at the helm.
Jason had been thinking about this distinction long before Asia, but after a week spent with more than a thousand leaders, it became much harder to ignore.
We keep talking about keeping a human in the loop.
His conclusion was stronger than that.
Humans shouldn’t simply remain somewhere inside a process designed around AI.
Humans should be at the helm.
“We're living in a magical time. We're living in a time where reinvention is calling our names as humans.”
It’s not up to the model.
It’s not up to AI.
It’s up to us.
Jason was clear about one thing before we wrapped the conversation: People Matters and Darwinbox deserve enormous credit for the experience they created across the week.
What stayed with him was the care behind the rooms, the conversations, and the way people were brought together and made to feel that they mattered.